HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Aminoquinoline → (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Aminoquinoline | HCID 11375 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-cyclopropylpropanamide | HCID 86685539 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide | HCID 86685540 | 43.9% |
Reaction Steps
A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-cyclopropylpropanamide (78 mg, 0.293 mmol), 3-aminoquinoline (60 mg, 0.416 mmol), K2CO3 (70 mg, 0.507 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 3 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)-3-cyclopropylpropanamide (48 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359308B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-f7265939afdb4a73b2488433752f54db |
| Source note | uspto-grants-2016_06 |